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Richard Dennis: The Trader & Teacher Behind the TurtleTraders

Nineteen eighty-six was a huge year for Richard Dennis. He made $80 million (about $147 million in 2007 dollars). That kind of money-making put him squarely at the center of Wall Street alongside George Soros, who was making $100 million, and then junk bond king Michael Milken of Drexel Burnham Lambert, who was pulling in $80 million.

Profits like those for Dennis came with heartburn. He was down $10 million in a single day that year before bouncing back, a roller-coaster ride that would have made mere mortals lose serious sleep. Yet Dennis cockily said that he slept like a baby during all that volatility.

His moneymaking style was about mammoth home runs and many smaller strikeouts. If there was a “secret,” he knew that you had to be able to accept losses both psychologically and physiologically. Still, 1986 was a long time ago, and memories dull when an old pro starts talking about the benefits of taking “losses.” During his heyday in the 1970s, 1980s, and mid-1990s, Dennis was described in a number of ways by those who knew of him. There was Dennis the legendary floor trader, Dennis the trading system’s trading guru, Dennis who started funds with investment bank Drexel Burnham, Dennis the philanthropist, Dennis the political activist, and Dennis the industry-leading money manager. He was a difficult man to stereotype, and he liked it that way.

“Dennis the gambler” was the only label that offended him, because he never considered himself a gambler in the Las Vegas sense. He understood financial Darwinism (read: “odds”) through and through. He always played the “game” knowing that everyone else was out to beat him. Financial futures pioneer Richard Sandor put Dennis in perspective: “The name of the game is survival when the markets are this chaotic. From that perspective, he may go down as one of the most successful speculators in the 20th century.”

Dennis’s success started long before he launched the Turtle experiment. He grew up in Chicago during the 1950s, a street kid from the old South Side neighborhoods. There was no privileged childhood with wealthy parents and well-placed friends. He did not have a silver spoon or the right connections.

The teenage Dennis was introverted and wore thick glasses and polyester pants. His first stab at trading, while attending the all-boys’ St. Laurence Prep School in Chicago, was to buy ten shares of a $3 “phonograph” stock. The company folded. While his first attempt at trading failed, he was a natural at poker, intuitively understanding the odds.

His teachers did not forget him. James Sherman, who taught theology and European history to Dennis, said that he never would take anything at face value. Dennis and his friends enjoyed the mental gymnastics of taking sides in an argument. Sherman added, “If some- body had said back then that Richard Dennis would become a very wealthy man as a commodity trader, I probably wouldn’t have believed them.” His former teacher would have predicted Dennis to be in front of the fire, with a sweater and a pipe, expounding on the cosmos.

At seventeen, Dennis landed a summer job as a runner ($1.60 an hour) at the Chicago Mercantile Exchange. Each day the exchange floor was mobbed by hundreds of traders fighting and screaming to place their trades. They were exactly like auctioneers buying and selling their wares except that they were in a trading pit battling it out. An indoor game of tackle football would be a good description of the scene. Dennis longed to be there, but to trade on the floor you had to be twenty-one. He found a way over that hurdle by talking his father into trading for him. A blue-collar worker for Chicago’s city government, the father became a proxy guided by his son’s hand signals from the sidelines. Despite some trading success in his teens, Dennis headed off to college at DePaul University, where his passion for philosophy (after flunking out of an accounting class) from high school days was re- kindled. He was most taken with British philosophers David Hume and John Locke, who had a relatively simple way of viewing the world. “Prove it to me” was their basic perspective.

Hume thought the mind a blank slate (tabula rasa) on which experience could be written. He believed that since human beings live and function in the world, they should try to observe how they do so. Dis- covering the causes of human belief was his key principle.6 Locke, on the other hand, argued that there were no innate ideas. He asked the question, “How is the mind furnished?” He wanted to know where reason and knowledge came from. His answer was one word: “experience.”

Both Hume and Locke belonged to the school of thought known as Empiricism. Empiricism is rooted in the notion that knowledge is derived from experiment, observation, and experience. Little nuggets of simple common sense from these two eighteenth-century British philosophers connected with an impressionable college student. They became his idols. Dennis was not shy about his leanings, asserting, “I’m an empiricist, through and through. David Hume and Bertrand Russell. I’m solidly in the English tradition.” Dennis saw Hume as ruthlessly skeptical. Hume took on the sacred cows of his generation, and Dennis loved that attitude.

It wasn’t only British philosophy that turned Dennis into a skeptic. Growing up in the late 1960s and early 1970s gave him an anti- establishment view of the world. He witnessed protesters being beaten by the Chicago police during the 1968 riots, right next to the venerable Chicago Board of Trade. It was a turning point in his life:

Trading has taught me not to take the conventional wisdom for granted. What money I made in trading is testimony to the fact that the majority is wrong a lot of the time. The vast majority is wrong even more of the time. I’ve learned that markets, which are often just mad crowds, are often irrational; when emotionally overwrought, they’re almost always wrong.

After graduating from DePaul University he received a fellowship to Tulane University graduate school, but promptly dropped out and returned to Chicago within days to start trading full time. Dennis bought a seat on the MidAmerican Commodity Exchange with money borrowed from his parents (part of it from a life insurance policy in his name). He still needed cash to trade, however. His initial war chest of $100 came from his brother Tom’s earnings delivering pizzas.

This was not a family of market operators. Dennis was always honest about his father’s “hatred” of the market, explaining, “My grandfather had lost all his money in the stock market in the Depression. The urge to speculate kind of skipped a generation.” He knew his father’s perspective would never work for him:

You can’t have a standard attitude about money and do well in this business. What do I mean by that? Well, my father, for in- stance, worked for the city of Chicago for 30 years, and he once had a job shoveling coal. So, just imagine coming from his frame of reference, and thinking about losing $50 in a few seconds trading commodities. To him, that means another eight hours shoveling coal. That’s a standard attitude about money.

It didn’t take long for his father to recognize Dennis’s unique abilities to make money. By the beginning of 1973, at twenty-four, Dennis had made $100,000. Around that time he cockily preached to the Chicago papers, “I just wanted to be able to get up and say, ‘I once made $100,000 a year, and I still think you are an ass.’ That rhetoric may not be wholesome motivation, but I do think it’s part of what drives me.” He was making so much money fast that whatever the context or content of an interview, it was outdated in weeks or even days.

A rebel at heart, Dennis cultivated being a character from the outset. He was fond of saying that he never liked the idea of sharing a birthday with Richard Nixon—a gentle stab at all those conservative traders surrounding him in the pits on LaSalle Street. He was an anti-establishment guy making a fortune leveraging the establishment, while wearing jeans.

Society was splintered during the time Dennis earned his first big money. Nineteen seventy-four was a difficult year in which to focus. What with G. Gordon Liddy having been found guilty of Watergate charges and the Symbionese Liberation Army kidnapping Patricia Hearst, it was a wild time of constant turmoil. To top it off, Richard Nixon became the first President of the United States to resign from office. Current events did not stop Dennis from leveraging a 1974 run-up in the price of soybeans to a $500,000 profit. By the end of the year, at age twenty-five, he was a millionaire. Even though he downplayed his success, he couldn’t hide it. When he showed up late one day to the soybean pit explaining that his beat-up 1967 Chevy had broken down, other traders gave him flack, knowing full well he could afford a new car hundreds of times over.

Not only was his persona different, his trading was different. Dennis read Psychology Today (no government economic or crop reports for him) to keep his emotions in check and to remind him of how over- rated intuition was in trading. He took delight in boasting, in contrast to most traders who got up early to read all they could from weather reports to daily Department of Agriculture assessments, that he stayed in bed until the last minute before getting to the exchange just as trading started. At one point during this time, Dennis was in the middle of an interview with a reporter as he went to the bank to make a deposit. He was depositing a $325,000 check (in 1976, that represented two to three weeks of work for him). Depositing an amount like that in the mid-1970s was not normal. Dennis always got hassled when he tried to deposit checks that size. He was oblivious to the fact that that the teller was looking at a check that likely would exceed her total career earnings. Yet Dennis, probably younger than she was, couldn’t sign his name straight.

As his notoriety continued to grow, national newspapers like the Chicago Tribune, the New York Times, and Barron’s trumpeted his youth and success. This was not standard operating procedure in a tight-lipped world where the big Chicago traders typically kept silent.

Dennis enjoyed and even reveled in his upbringing and the unique perspective it afforded him:

I grew up in an Irish-Catholic family on the South Side of Chicago. My institutional values were very strong, if somewhat con- fused. My holy trinity consisted of the Catholic Church, the Democratic Party, and the Chicago White Sox. I would describe my early value system as nourishing, if limited. When my father took me to Hurley’s Tavern, I saw people falling off their bar stools—about what you’d expect from people who called whiskey “Irish pop.”

The Church, baseball, Democratic politics, and Irish drinking weren’t only an influence on his youth:

How much of my holy trinity informs me as an adult? In the White Sox I have a deep and abiding faith. In the Democratic Party I have shallow and fading faith, which is almost never re- warded. In the church, well…I fear 16 years of Catholic education left me a skeptic.

Look at that 1976 New York Times photo of the then twenty-six- year-old multimillionaire, lounging on the couch with his dad seated to his left, seemingly oblivious to the photographer, and it is easy to see anti-establishment staring into the camera. The photo caption only reinforced Dennis’s differences: “He drives an old, inexpensive car, he dresses in cheap knits; his money tends to pile up, unused.” However, all this press at such a young age left Dennis confronted by something he probably wasn’t expecting: people with their hands out, asking for money. “Most of them were very sad,” he recalled. “One person said, ‘Help me to learn how to trade. I’m in debt.’ Some people made it sound as if $5,000 or $10,000 were all they needed to make them happy. Those were the only letters worth answering—to explain that money won’t really make a difference.”

Not many twenty-six-year-olds would have been mature enough to handle the press using such folksy wisdom. Yet Dennis never let the swirl around him interfere with what he was doing to make money. Quite simply, his trading technique was to trade seasonal spreads. In other words, he wanted to take advantage of seasonal patterns in markets like soybeans—his initial specialty. Dennis would hold “long” (bets to profit as the market increased) and “short” (bets to profit as the market decreased) positions in futures contracts simultaneously in the same or related futures markets.

The MidAm Exchange Experience

Once he had his MidAm seat (formerly called the Chicago Open Board), Dennis was off and running. Initially he had no clue what he was doing, but he was a fast learner who learned to think like a casino operator: When I started out, I had a system called “having no idea whatsoever.” For four years, I was just taking edges. If someone was giving me a quarter cent edge to buy an Oat contract, I didn’t think he knew anything either. I just knew that I was getting a quarter cent edge, and at the end of the day, the edges would approximately equal my profit. Obviously, on an individual basis that doesn’t have to happen, but over a longer period of time, it will. I tried to be like the house in the casino. It wasn’t that novel. People at the Board of Trade had been doing it forever. But for the MidAm, it was kind of revolutionary because no one would understand that you could balance your risk with a lot of volume. That’s how I started. Dennis went from zero to sixty on the MidAm in record time, and no one knew how he learned to do what he was doing. He knew that traders had a tendency to self-destruct. The battle with self was where he focused his energies: “I think it’s far more important to know what Freud thinks about death wishes than what Milton Friedman thinks about deficit spending.” Go down to Wall Street today after work with the hot-shot traders all earning $500,000 a year at the big banks and you’ll find very few who talk about Freud being the ticket to making millions.

However, trading was harder than Dennis let on. The early ups and downs took a toll on him, but he learned the hard lessons within months. “You have to have mentally gone through the process of failure,” he said. “I had a day during which I made every mistake known to modern man. I took too big risks. I panicked and sold at the bottom of every break. I had built my net worth up to about $4,000 coming into that day and I lost about $1,000 in two hours. It took me about three days to work through that experience emotionally, and I think it was the best thing that ever happened to me.”20 It was about this time, in 1972–73, that fellow traders Tom Willis and Robert Moss met Dennis. They would go on to work together for years as close friends and business associates, with Dennis as their leader. The star did not wear a polished Armani suit, nor did his bud- dies. They sported used-car-salesman jackets, with muttonchops and bad hair, but their appearance disguised calculated gamers looking to beat the pants off their peers every day of the week. Willis, like Dennis, was brought up in a working-class family. His father, who worked first as a milkman and then delivering bread, helped him buy a seat on the MidAm for $1,000 at age twenty-one. Willis had never heard of the exchange until he saw an article in the Chicago Tribune with the headline “Altruistic Grain Trader Successful.” It was about 22.5-year-old Richard Dennis.

Willis immediately identified with his peer’s anti-establishment way of viewing the world. Dennis was not afraid to say that he had voted for Eugene McCarthy and didn’t think that just because he had radical ideas he should be driving a cab. Years later, Dennis was even more direct, saying that “the market was a legal and moral way to make a living. Being a trader doesn’t oblige one to be a conservative.”

Yet Dennis’s political stance was not what first caught Willis’s attention; it was his attitude about making money in a world where class and distinction were always barriers to entry. Without a second thought, Willis hopped in his Jeep and drove to the Fisher Building in the Chicago Loop to check out the exchange. When he arrived at the MidAm for the first time, his soon-to-be role model dominated the landscape: “Rich was in the pit. I knew him by the photo from the Tribune.” Willis started trading with his MidAm seat, but had no immediate contact with Dennis even though they were the two youngest traders in the pit. Nearly everybody else was sixty-five to eighty years old, and they actually had chairs and spittoons in the trading pit. A young Dennis, towering above a sea of old guys lounging on chairs, must have been a sight. Situated only a few blocks from the Chicago Board of Trade, the MidAm was a bit player at the time. It was small, perhaps fifteen hundred square feet. While Willis didn’t know how his start at the MidAm would unfold (he ended up building a thirty-plus-year trading career), he was certain Dennis saw a much bigger future.

Even then, big wigs from the Chicago Mercantile Exchange (CME) were coming over in their limos to pick young Dennis’s mind. Ultimately, Dennis approached Willis most likely because he was good enough not to go broke and because they were both about the same age. Dennis told Willis, “If you’re buying wheat and it’s strong and the beans are too low and the wheat is five higher, why don’t you sell soy- beans instead of selling the wheat you bought?” It was a very sophisticated insight. In fact, buying “strength” and selling “weakness” short still befuddles investors. It is counter-intuitive to buying low and selling high.

Dennis was already sharing his knowledge with other traders. He was a natural-born teacher. Dennis was teaching the young exchange members at either his or Willis’s apartment. Willis would buy two hundred pieces of chicken and a barrel of potato salad. There were fifty or sixty guys in his one-bedroom apartment with Dennis holding court, explaining how to trade. There was a practical need for this. The MidAm was selling new memberships to all kinds of traders, many with no experience. Dennis and Willis were teaching “liquidity.” To give the market confidence in the viability of the MidAm exchange, there had to be a critical mass of buyers and sellers. This culture of education was creating a better ex- change with better traders. And those better traders were starting to make money. It could all be traced to Dennis.

Craig and Gary Lacrosse, Ira Shyman, John Grace, Wayne Elliott, Robert Tallian, and David Ware are all Chicago traders who learned from Dennis. While they may not be household names, they became hugely successful in part because of the generosity of the young Dennis, who felt no compunction about sharing his skills with others. After the apartment-training sessions everyone would go home, and they would meet the next day in the pits. During market hours they would ask Dennis, “Is this what you meant?” and he’d say, “Yeah.” Dennis freely gave away his knowledge.

The Chicago Board of Trade

Great experiences and profits aside, it wasn’t long before Dennis needed a bigger playing field than the minor-league MidAm. He was already plotting how to beat the big boys at the Chicago Board of Trade (CBOT), the world’s largest futures exchange. Once at the CBOT, his placid demeanor contrasted sharply with the hoarse shouts and wild gestures of other floor traders, many of whom were millionaire traders with decades of experience. He was soon beating them at their own game with a “betting” style that was often so relaxed that his trading cards would literally slip out of his hand onto the floor.

Dennis’s move to the CBOT was historic. Willis could hardly believe it: “Richard goes to the Board of Trade and knocks the cover off the ball. They’ve never seen anything like this. I mean this kid takes the whole pit off. Not because he can or not because he wants to show off, but corn is up, beans are up two and the corn is down three and they sell him a million bushels of soybeans up one and a half and the next thing you know they close up seven and they’re talking about him, ‘Who’s this new kid?’ ” Willis refrained from divulging the names of old-timers that Dennis was beating the pants off when he first hit the CBOT, since many of those losing traders are still around today.

One of Dennis’s students said that their teacher believed his physical attributes to be behind his pit-trading success: “You ever heard why he considered himself really successful? He is six feet something and the size of a freight train. He could see over people and more importantly, people could see him. People always knew that he was there. He honestly felt that’s why he was successful.”

Dennis’s attributing his height and weight as the reason he was successful is not the full story. There was more to becoming a millionaire by twenty-five than being “six foot something” and three hundred pounds plus. Even with excess weight, his peers described him as having cat-quick reflexes on the trading floor.

The Move from the Pit

Trading on the floor, down in the pit, might have been exciting during this era, but today the Chicago Board of Trade floor is silent. That doesn’t mean trading is dead today—far from it. Electronic trading out- dated the old ways faster than anyone ever thought could happen. However invigorating the trading floor may have been in the 1970s, the only way for Dennis to expand his trading success was to move away from it. The Chicago trading floors were designed with multiple pits and each pit traded a different market. To trade more than one market, he had to physically move back and forth across the floor to the various pits.

Dennis’s solution allowed him to remain faithful to buying in strength and selling in weakness. He knew that if his system worked in soybeans and corn, then it would also work in gold and stocks and all other markets. At the same time, he saw Wall Street changing, with new markets appearing fast and furiously as economies around the world opened and expanded. Fixed income futures were launched, and by 1975 the Inter- national Monetary Market (IMM) was allowing anyone to trade currencies the way they did stocks. Dennis knew what this would all mean. To trade in that bigger world, Dennis moved into an office on the twenty-third floor of the CBOT, leaving the turmoil of screaming traders behind. Concurrent with his move, in November 1975, Dennis and Larry Carroll formed a partnership. Known simply by the first initial of their last names, C&D Commodities was born.

There is little public information on Larry Carroll (they did meet on the MidAm floor). And, although Dennis’s “D” came second, theirs was not a partnership where the decisions and profits were split fifty- fifty. Dennis was always the man. Within short order, C&D Commodities became one of the largest independent trading firms in the world. They quickly rivaled such established institutional investors as Salomon Brothers and the Pillsbury Company.

However, other traders who had seen him dominate the pits were shocked when Dennis left the floor. They thought he was crazy. To compete against the likes of Pillsbury and Salomon Brothers was considered suicide, because no one thought he could maintain that floor “edge.” Dennis himself had always said the pit was the safest place to be. The transition did almost sink Dennis. When he went off floor, he struggled. In the late 1970s, the markets were getting to him. Tom Willis saw the struggle and recalled, “He was a little disillusioned, a little off balance frankly.” Both men went out to a bar to discuss the situation. Dennis was not throwing in the towel. He looked at Willis and said, “Tom, I got stuff that’s so good that used off floor in the right hands it would make $50 million a year.”

In today’s terms, this would be like someone saying he has a way of trading that’s so good he can make $200 million a year. Or think of some number that is fifty times more than is rationally achievable by any normal measure. With anyone else, Willis would have been skeptical: “If I didn’t know Rich. I would have said, ‘Gee, he really does sound a little more off balance than I’m even thinking.’ Saying $50 million in 1979 is a crazy thing to do, but I believed it. And he did it. If an edge is good or the idea is good, let’s get in front of the screen and trade them all. If it’s that good, let’s get in front of the screen and have 20 people do this. As a matter of fact, it’s very, very consistent to expanding geometrically the ability to take advantage of this good idea.”

The goal of trading every market he could and making more money in the process was reached within a year, just as Dennis had predicted. Yet making that much more money didn’t change him one bit. His new office was not marble and glass. The outside hallway to the office had dingy brown paneling. On his office door was “C&D Commodities, Richard J. Dennis and Company.” No flash. The men’s room for the floor was next door.

Martin Hare, a nephew of Larry Carroll’s, was sixteen and in high school when he was working for Dennis. Now an executive with Merrill Lynch in San Diego, he worked in Dennis’s unconventional office environment from 1982 to 1989. Hare still gets enthusiastic when he thinks about his after-school job: “I cut out the Wall Street settlement prices for three summers. My weekly salary at C&D was $120. That was up from $90 the summer before. The C&D office was royal blue in color. There was a sleeping room for those that needed to nap, mostly for Rich, and a refrigerator full of the best beer.”

Dennis may have physically disappeared from the trading floor, but the hermit-like trading wizard hovered over the markets like Zeus. Everyone knew he was there when a huge order came into the pits. Traders also knew not to get in front of his orders, or they could be potentially wiped out. Critics and regulators at times thought he was too big and moved markets unfairly. Dennis scoffed, “Sour grapes.”

The criticisms were an excuse for people who had learned to lose. Dennis had no patience for people targeting his success. “I cringe a little when I’m identified as a millionaire,” Dennis said after reading that his $250,000 contribution to Adlai Stevenson was the largest individual political gift ever in Illinois. “If somebody just had $100,000, he wouldn’t be called a thousandaire, and if a pauper gave a dollar, they wouldn’t say, ‘Pauper gives his last buck.’ ” Although he grew wealthier by the day, he still kept an antinuclear poster hanging in his office and remained outside the chummy atmosphere of the exchanges. He was not prone to travel in the limelight. “We don’t have much contact with him,” remarked one Board of Trade player.

While his peers collected vintage cars and mansions, Dennis kept wearing those out-of-date polyester pants hiked over an ever-expanding waist. He exercised by eating cheap hamburgers at noisy grills. Dennis in a short-sleeved shirt, no tie, religiously pouring over arcane base- ball statistics from the Baseball Abstract, was a common sight. In fact, he would eventually buy a piece of the White Sox baseball team. Once he was an owner, his 1980s attempt to get White Sox management to see the benefits of Bill James–style “Moneyball” fell on deaf ears. One of his students, Michael Shannon, watched his friends try to dress him up by moving him from his South Side studio apartment, and recalled, “Bill Eckhardt and others actually forced him to move into something that was a little bit more parallel to his station.”

Money for Dennis was just a way to keep score in the game. He was frank about it: “Trading is a little bit like hitting a ball. If you’re thinking what your batting average should be, you’re not concentrating on the right thing when you bat the ball. Dollars are the batting average of the trader.” This original thinker and big-time baseball fan left a visual image on everyone. Several confidantes talked about Dennis’s socks. One of his students smiled, “You need to make sure he’s wearing a matched pair of the same color.”

Bradley Rotter, a former West Point graduate and often called Dennis’s first investor, witnessed his eccentricity: “I was at his house for a Fourth of July tennis party and Richard Dennis couldn’t be found…at the end of the party he came out of his house wearing a white tennis shirt, white tennis shorts, and black shoes and black socks. I’ll never forget that picture.” Rotter was not mocking Dennis. He respected Dennis’s testicular fortitude to trade trends no matter what. In baseball, testicular fortitude means everyone can talk about the game, but if you’re going to get into the game, you must swing the bat. Dennis swung and swung hard. No singles. His was Babe Ruth, home-run, swing-for-the-fences-style moneymaking.

However, the Babe Ruth of trading was near oblivious to the basics of everyday life. Mail and personal bills were handled by C&D’s back office because of his inattention. His office would even send over toilet paper to his apartment. The weight room in his Gold Coast condo was virtually unused. “I pat the weights once in a while.” said Dennis. He enjoyed using a third of his time to do absolutely nothing. Another Dennis student, Erle Keefer, went beyond his eccentricities: “Rich is probably the greatest trigger puller that I personally have ever known: he has the ability under tremendous pressure to stand there with his own money and pull the trigger when other people wilted. And when he was wrong, he could turn on a dime. That’s amazing—that’s not trading, that’s genetic.” The genetic line was debatable; after all, that was the point of his Turtle experiment.

Dennis’s success eventually caused more serious problems. In the mid- 1980s, critics accused him of strong-arming the market. They blamed him for too much market volatility. Words like “collusion” were thrown around. Dennis was not buying it. He said, “One man’s volatility is another man’s profit.” When Dennis was a guest on a radio show in 1984, a caller assured him that if he traded long enough, he would give it all back. You could feel the anger. Some people simply did not want to hear about a young guy making millions. Even though everyone knew exchanges needed speculators, too many people didn’t want those same risk-takers to make a profit. Dennis himself appeared before Congress as they investigated the “efficiency of the markets”—unable to define what that phrase meant. His detractors were silenced after government regulators testified that the total buying and selling by Dennis did not breach exchange limits.

Soon, Dennis would join the political fight at a whole new level. He became one of the largest Democratic donors in the country, often focusing his generosity on standard politicians and assorted underdogs. From donating millions to battered women’s shelters to the decriminalization of marijuana, causes without wide publicity appealed to him (he would give away 10 percent of his earnings every year). While calling himself a liberal libertarian, he once donated $1,000 to former Black Panther Bobby Rush.

Dennis did more than just write checks. He became good friends with Bill Bradley and supported Walter Mondale (1984) and Bruce Babbitt (1988) for President. He lobbied hard against conservative stalwart Robert Bork. There was a rational justification in Dennis’s mind for his political ideals: “If it’s something everyone hates but you think is right, those are the important things to do because no one else is going to do them.”

However, becoming a successful politician on the basis of supporting the have-nots of society was not as easy as trading to make millions. It wasn’t enough merely to fund his causes; Dennis also wanted to “work” them, and immediately ran into roadblocks. Politics was not a zero-sum game, and he got frustrated. “Politicians, at worse, are mindless replicas of what their constituents think. People…don’t want to hear painful truths.”

When invited to participate in the diplomatic dances that made up Washington politics, he stepped on toes, and seldom refrained from voicing his opinions. Former Federal Reserve chairman Paul Volcker was once introduced to Dennis. He told Dennis that he didn’t “like those casinos you have out there in Chicago.” Dennis was well aware that he was being indulged because he was rich and would be listened to only if he had something significant to say. Soon after he founded his new 1982 think tank, the Roosevelt Center for American Policy Studies in Washington, D.C., it began to flounder.

Washington was a tough market no matter how many millions you had. And now Democrats were frustrating him, too. He said, “My principal irritation with liberals in general: they don’t understand how it can possibly be true that you make the poor richer by making every- one richer. I don’t understand that they don’t even consider that possibility.” The problem in a political world was that Dennis couldn’t work the floors of Congress the way he had the Chicago trading floors. It was one thing to own one of the six original copies of the U.S. Constitution (which he did) and an entirely different thing to try to influence modern political leaders. He was impatient.

Ultimately, over time he would become a board member of the libertarian Cato Institute, serving with such notable peers as John C. Malone, chairman, Liberty Media Corporation, and Frederick W. Smith, chairman and CEO, FedEx Corporation. He also joined the board of the Reason Foundation, another libertarian think tank. Dennis’s political forays were never easy. One political critic of his thought Dennis was a bully because he didn’t adjust his thinking to accommodate others. Dennis saw that criticism as coming from a typical Washington careerist being afraid to rock the boat.

His stance on the decriminalization of narcotics best illustrated what made him tick. He knew the “drug czar” of the day, Bill Bennett, would never defeat drug violence with his “just say no” approach. Dennis thought people should be allowed to do what they wanted to do, even if they injured themselves, as long as they did not hurt others. He commented:

The drug war violates the Golden Rule of doing unto others as you would have them do unto you. None of us is free of vice or temptation. Does any one of us really want to be jailed for our moral shortcomings? If our teenaged child is arrested for drug possession—a distinct possibility, since 54 percent of teenagers admit trying illicit drugs—do we really want him or her sent to prison for falling victim to the curiosity of youth?

Here was a man making millions in the pits by winning as much money from others as possible, but at the same he was clearly worried about others’ well being. He was a mass of contradictions.

Rough Seas

Dennis had some severe down periods before that banner year of 1986. Perhaps his political ambitions had caused a loss of focus. Adding to his responsibility, by this time he had moved beyond trading only his own money. He was trading for others, and managing their money was not his strongest suit. He said, “It’s drastically more work to lose other people’s money. It’s tough. I go home and worry about it.”

This was not what his clients wanted to hear. In 1983, when his as- sets under management peaked at over $25 million, his accounts for clients hit turbulence. After a 53 percent rise in January, accounts dropped 33 percent in February and March. That drop was enough to prompt George Soros to yank the $2 million he had invested with Dennis only two months earlier. After a partial rebound in April and May, Dennis’s funds dived another 50 percent in value. His 1983-era computer that cost $150,000 did little to console nervous clients. It took many of his investors more than two years to get back to even with their investment. Most didn’t stick around, and Dennis closed down some accounts in 1984. He rebated all management fees to losing accounts and conceded that trading client money as aggressively as his own money was not something clients could psychologically handle.36 What did that aggression look like on a month- by-month basis?

Dennis was famous for those big returns, and that was what his clients wanted—to become rich like Rich. They got on board knowing full well the voyage would get rocky, but conveniently forgot that fact when rough sailing made them seasick. At the first sign of troubled waters, when they were puking losses, they cut short the voyage and blamed Dennis. He was learning the hard way about people’s irrational expectations.

In 2005, Dennis looked back on his troubled times in the fund management arena:

I think the problem is that a money manager very rarely ever sits down with the person whose money it is. There’s always a representative of a firm of a firm of a firm. When you have customer money, you generally try to please the people who want “pass- able,” whereas you might be able to explain it to the ultimate end user whose money it is that “this might look brutal, but we’re trying for something spectacular.”

However, at that time in 1983, Dennis needed a way out of the customer rat race. He wanted to divert even more attention to big-picture strategies, from philosophizing to an even greater focus on decriminalization of pot to anything but being beholden to impatient and uninformed clients.

In many ways his Turtle teaching experiment was his second act, and he knew it. He said, “You shouldn’t, I suppose, live in your trading children’s reflective glory, but I am. I think [training the Turtles] is the single best thing I’ve done in commodities.” Yet there was no way he could have known at the time that the single best thing he would do would change his life and the history of speculative trading in ways never imagined. Glory and legend aside, in 1983, with a clear plate, Dennis’s most immediate task was to select his Turtle students from the thousands who responded to his want ad.

Final thought from Dennis:

“I don’t think trading strategies are as vulnerable to not working if people know about them, as most traders believe. If what you are doing is right, it will work even if people have a general idea about it. I always say you could publish rules in a newspaper and no one would follow them. The key is consistency and discipline.”

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